Cole painted this and its pendant Summer Twilight, A Recollection of a Scene in New England (1858.46) while he was in the early stages of creating his monumental five-painting series The Course of Empire (1858.1-5). That series traces the rise and fall of an imaginary civilization, and in this pair Cole prefigured the larger themes of the series, but he placed them in an unmistakably American context.

The critic and painter William Dunlap recalled visiting Cole in his studio on November 15, 1834 and seeing "2 small jewells [sic] & 2 larger paintings being the first two of the sett [sic] of 5 for Luman Reed Esq." The two large works were The Savage State (1858.1) and The Arcadian or Pastoral State (1858.2), which begin The Course of Empire series. The two "small jewells" [sic] were these seasonal twilight scenes, which closely parallel the themes of their larger counterparts. Cole clearly intended them as a pair: they are the same size and retain their identical original frames. Cole exhibited them together at the National Academy of Design in 1834, perhaps as a preview of his series.

Autumn Twilight depicts Mount Chocorua in its richest autumnal finery. The scene is untouched by any trappings of civilization; in the foreground a storm-blasted tree trunk has been violently disfigured by the ungovernable power of nature. At the lower right an Indian glides by in his canoe, gazing steadily at the viewer as if in warning as he departs the scene. It bears a close relationship to the The Savage State, another wild landscape inhabited only by aboriginal figures.

Cole purposely titled this painting with a specific location, which, along with the Indian figure, would have brought to any contemporary viewer's mind the legend of Chocorua. The story evolved throughout the late eighteenth and early nineteenth centuries, but in its most basic form, the Indian Chocorua was pursued to the mountain summit by a group of white men (for reasons that vary in different accounts) and leapt to his death, but not before uttering a curse on the land, which was later blamed for the high mortality of cattle who grazed near the foot of the mountain.

Cole's interpretation of the story showed his sympathy for the Indian, relating how the white men "gave the poor despairing and defenceless [sic] wretch the cruel choice of whether he would leap from the dreadful precipice on the top of which he stood or die beneath their rifles." Cole was moved to depict the crucial moment in his 1828-29 The Death of Chocorua, which is not currently located, but survives in the form of an engraving. In the N-YHS's Autumn Twilight of five to six years later, Cole referenced Chocorua's curse indirectly and used it as a point of departure for his own "legend" showing the uncorrupted origins of civilization that he would elaborate upon in The Course of Empire.

"From Colony to Nation: 200 Years of American Painting at the New-York Historical Society," New-York Historical Society, June 7 - September 8, 2013."The Course of Empire: Thomas Cole and the Hudson River School Landscape Tradition," New York State Museum, Albany, NY, August 23-November 30, 2003.